Methanol → 2-(6-Methoxy-2-naphthyl)propionic acid

HRID 482160Notes

Reaction equation

HRID 482160 reaction equation
[OH-].[K+].CO.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[CH:11]=[CH:10]2>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 2732945ethyl 2-(6-methoxynaphthalen-2-yl)propanoate

Product 1

HCID 13022-(6-Methoxy-2-naphthyl)propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To the benzene solution of bis(6-methoxy-2-naphthyl)zinc formed in Example 61 above is added 9.96 grams of ethyl 2-bromopropionate in 5 mL of anhydrous benzene. The temperature of the reaction mixture is maintained at from 50° to 55° C. for 15 hours, under nitrogen, and then the reaction mixture is mixed with 175 mL of 1.5N hydrochloric acid solution, followed by 65 mL of methylene chloride. The mixture is filtered, and the organic phase is separated. The aqueous acid layer is extracted with two further 30 mL quantities of methylene chloride, and the methylene chloride extracts are combined, washed with 50 mL of water, and stripped of solvents under vacuum to yield ethyl 2-(6-methoxy-2-naphthyl)propionate. A solution of 6.0 grams of potassium hydroxide, 6 mL of water and 60 mL of methanol is added to the ethyl 2-(6-methoxy-2-naphthyl)propionate, and the mixture is heated at reflux for 45 minutes, cooled to ambient temperature, acidified and mixed with 60 mL of water. Methanol is removed by evaporation in vacuo, and the resultant solution is extracted with two 60 mL portions of methylene chloride. The combined methylene chloride extracts are evaporated to dryness to yield 2-(6-methoxy-2-naphthyl)propionic acid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 45 minutes
  3. customMethanol is removed by evaporation in vacuo
  4. extractionthe resultant solution is extracted with two 60 mL portions of methylene chloride
  5. customThe combined methylene chloride extracts are evaporated to dryness

Sources & evidence

ORD record
ord-58f0a2768e0443589d3a5e4eda73c7b7
Source dataset
uspto-grants-1998_08
Patent number
US05792886

Reaction notes

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